New azodyestuffs



Patented Sept. 27, 1932 UNITED STATES PATENT oFncE MAX HARDTMANN, or NAUNHOF, NEAR LEI'PZIG, GERMANY, AssieNoR To GE ERAL ANILINE WORKS, INC., 01 NEW YORK,

N. 2., A CORPORATION OF DE AWARE EW AZODYESTUFFS e No Drawing. Application filed December 23; 1931,

The present invention. relates to new azodyestuil's, more particularly it relates to dyestuffs which maybe represented by the probable general formula;

a H: wherein the benzene nucleus B may be substituted by a sulfonic acid group, 00 stands for hydrogen, alkyl, alkoxy or halogen and y stands for hydrogen or the groups i r I OOH new dyestuffs are obtainable by diazotizing in the usual manner with sodium ni- Serial No. 582,873, and in Germany January? 1931; I

Fromthe solutiontheazodyestufi's are sep arated in the usual'inanner vby saltingout,

filtered and dried aI-n form'oi their alkali; metal salts they Laregenerally yellowishpow ders, solublein -water,-dyeing the vegetable I fibre yellow shades which by after-treatv ment with a suitable copper compound, such as copper sulfate, become very fast to light:

" and washing. The invention is illustrated by the follow- 1 ing examples, withoutbeing limited thereto: 7 Example 1.217 parts by weight of 4-sulfo 2-aminobenzoic acid are diazotized in the usual manner with sodium nitrite and hydrochloric acid. The dia-zo solution thus ,obtained is introduced into a sodaalkaline solutionprepared froin .190 parts by weight of diac etoacetyl-o-tolidine, While stirring. When .the coupling is complete, thed'yestuff is salted out, filtered with suction 'and dried. Inits free state it has the following formula:

coon

Hots

When treating cotton dyed with the 1 dye stuif'thusprepared' in an aqueous copper sulfate solution a greenish yellow .ofl excellent fastness to light and washirigis obtainedr? By substituting the t-sulfo-Q-aminobenzoic acid by the 5-sulfo-2-laminobenzoic acid, somewhat more reddish shades areobtained. Likewisetherefis-obtained a more reddish shade by substituting the diacetoacetyl-o-tolidine by the diacetoacetylbenzidine or by the diacetoacetyl-o-anisidine. o

By substituting the diacetoacetyl-o-toli dine by the diacetoacetyl-o-chlorobenzidine a more greenish is obtained.

, til

The dyestufi dyes cotton greenish yellow (sihzfiies which by coppering become somewhat I claim:

1. As new products the azodyestuffs having in their free state the probable general formula:

weight of 4-sulfo-2-aminobenzoic acid are introduced with stirring. When the coupling GOOH wherein the benzene nucleus R may be substituted by'a sulfonic acid group, an stands is complete, excess soda is added and a diazo for hydrogen, alkyl, alkoxy or halogen and y solution prepared from'68 5 parts by weight of 2-Vaminobenzoic acid are introduced. When the coupling is complete, the dyestufl' is isolated in'the usual manner. In its free state it'has the following formula:

COOH

coon

azo compoundprepared from 108.5 parts by weight of 5-sulfo-2-aminobenzoic acid in acetic acid solution, there is obtained a dyestuff having in its free state the following formula:

CHr-C 0-?11-0 O HN NH-C O-GHrC O-CH3 N V 1% H10 I 7 stands for hydrogen or the'group II N being in form of their alkali metal salts water soluble yellow powders, dyeing the vegetable fibre yellow shades which by aftercoppering become fast to washing and light.

2. As a new product the dyestuff having in its free statethe following formulaz- COOH being in form of its alkali metal salts'a water soluble yellow powder, dyeing the vegetable fibre yellow shades which by aftercoppering become fast to washing and light.

3. As. a new product the a'zodyestufi' hav ing in its free state the following formula:

COOH OOH water soluble yellow powder, dyeing the vegetable fibre yellow shades which by aftercoppering become fast towashing and light. 7 4. As anew product the azodyestufi' having in its free state the following formula:

OOOH

being in form of its alkali metal salts a water soluble yellow powder, dyeing the vegetable fibre greenish-yellow shades which by aftercoppering becomes fast to washing and light. In testimony whereof, I affix my signature.

MAX HARDTMANN.

Certificate of Correction Patent No. 1,87 9,223. September 27, 1932.

MAX HARDTMANN It is hereby certified that error appears in the printed specification of the abovenurnbered patent requiring correction as 011 mm: Page 2, after line 55, strike out the formula and insert instead- E me as OCOOH and that the said Letters Patent should be read with this correction therein the the same may conform to the record of the case in the Patent Office.

Signed and sealed this 27th day of December, A. D. 1932.

[sEAn] M. J. MOORE,

v Acting Cowmvissioner 0 7 Patents. 

